Assignment of (6R*,10R*)-relative stereochemistry to the major component of the sex pheromone of the maritime pine scale, matsucoccus feytaudi
✍ Scribed by Kenji Mori; Susumu Harashima
- Publisher
- Elsevier Science
- Year
- 1991
- Tongue
- French
- Weight
- 233 KB
- Volume
- 32
- Category
- Article
- ISSN
- 0040-4039
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The sex pheromone of Matsucoccus matsumurae Japanese pine bast scale (2E,4E)-(6R,10R)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one (1) was synthesized with stereocontrol from (2R,4S)-5-acetoxy-2,4-dimethyl-pentanol (3), which in turn was prepared by lipase-catalyzed transesterification of meso-2,4-di
## Abstract (3__S__,7__R__,8__E__,10__E__)‐3,7,9‐Trimethyl‐8,10‐dodecadien‐6‐one (1), the major component of the female‐produced sex pheromone of the maritime pine scale (__Matsucoccus feytaudi__), was synthesized by starting from epoxide 2, which was obtained from __meso__‐__epoxy__ diacetate (F)
butoxycarbonyl-2-methylpropanoic acid (D) and (2R,6S)-7acetoxy-2,6-dimethyl-1-heptanol (G), by employing lipase-dodecyl propanoate (1 and 2), the components of the pheromone of Microdiprion pallipes, were synthesized from catalyzed kinetic resolution in a later step. two chiral and nonracemic buildi
## Abstract A new synthesis of (2__E__,4__E__,6__R__,10__R__)‐4,6,10,12‐tetramethyl‐2,4‐tridecadien‐7‐one (1; matsuone) was achieved by starting from (2__R__,3__S__)‐4‐(__tert__‐butyldiphenylsilyloxy)‐2,3‐epoxy‐1‐butanol (21 = E) and methyl (__R__)‐3‐hydroxy‐2‐methylpropanoate (2 = I). Cleavage of